(4-methoxyphenyl)methyl (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-3-[3-[(3S,4S)-3-methyl-4-[(2-nitrophenyl)sulfonylamino]-5-oxo-5-[(2-oxo-2-phenylmethoxyethyl)amino]pent-1-yn-3-yl]oxy-4-phenylmethoxyphenyl]-2-[methyl(phenylmethoxycarbonyl)amino]propanoate | 1297295-85-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4-methoxyphenyl)methyl (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-3-[3-[(3S,4S)-3-methyl-4-[(2-nitrophenyl)sulfonylamino]-5-oxo-5-[(2-oxo-2-phenylmethoxyethyl)amino]pent-1-yn-3-yl]oxy-4-phenylmethoxyphenyl]-2-[methyl(phenylmethoxycarbonyl)amino]propanoate
• CAS: 1297295-85-2
• 化学式: C₆₀H₆₆N₄O₁₅SSi
• 分子量: 1143.35
• InChiKey: VOUCHGYUKGJTPS-APUFSFBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  81
• 可旋转键数：
  30
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  249
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (4-methoxyphenyl)methyl (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-3-[3-[(3S,4S)-3-methyl-4-[(2-nitrophenyl)sulfonylamino]-5-oxo-5-[(2-oxo-2-phenylmethoxyethyl)amino]pent-1-yn-3-yl]oxy-4-phenylmethoxyphenyl]-2-[methyl(phenylmethoxycarbonyl)amino]propanoate 在 碳酸氢钠 、 1-羟基苯并三唑 、 caesium carbonate 、 苯硫酚 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (4-methoxyphenyl)methyl (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-3-[3-[(3S,4S)-3-methyl-4-[[(2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]-5-oxo-5-[(2-oxo-2-phenylmethoxyethyl)amino]pent-1-yn-3-yl]oxy-4-phenylmethoxyphenyl]-2-[methyl(phenylmethoxycarbonyl)amino]propanoate
  参考文献：
  名称：

  Structure–activity relationships of ustiloxin analogues

  摘要：

  Four novel ustiloxin D analogues were synthesized focusing on the size of the macrocyclic core, the stereochemistry at the bridgehead ether, and the enantiomer of ustiloxin D. All four were subjected to biological evaluation testing the inhibition of tubulin polymerization. Only 2,2-dimethyl-ustiloxin D retained any activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.165
• 作为产物：
  描述：

  (2R,3S)-3-methyl-2-(2-nitrobenzenesulfonylamino)-pent-4-yne-1,3-diol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium chlorite 、 H₂O₄P^(1-)*Na⁽³⁺⁾ 、 1,5,7-三氮杂双环[4.4.0]癸-5-烯 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 33.0h， 生成 (4-methoxyphenyl)methyl (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-3-[3-[(3S,4S)-3-methyl-4-[(2-nitrophenyl)sulfonylamino]-5-oxo-5-[(2-oxo-2-phenylmethoxyethyl)amino]pent-1-yn-3-yl]oxy-4-phenylmethoxyphenyl]-2-[methyl(phenylmethoxycarbonyl)amino]propanoate
  参考文献：
  名称：

  Structure–activity relationships of ustiloxin analogues

  摘要：

  Four novel ustiloxin D analogues were synthesized focusing on the size of the macrocyclic core, the stereochemistry at the bridgehead ether, and the enantiomer of ustiloxin D. All four were subjected to biological evaluation testing the inhibition of tubulin polymerization. Only 2,2-dimethyl-ustiloxin D retained any activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.165

文献信息

• Structure–activity relationships of ustiloxin analogues
  作者：Madeleine M. Joullié、Simon Berritt、Ernest Hamel

  DOI：10.1016/j.tetlet.2010.11.165

  日期：2011.4

  Four novel ustiloxin D analogues were synthesized focusing on the size of the macrocyclic core, the stereochemistry at the bridgehead ether, and the enantiomer of ustiloxin D. All four were subjected to biological evaluation testing the inhibition of tubulin polymerization. Only 2,2-dimethyl-ustiloxin D retained any activity. (C) 2011 Elsevier Ltd. All rights reserved.